Cesium fluoride → Methyl 3-chloro-4-(2,4-difluorophenyl)quinoline-6-carboxylate

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Reaktionsgleichung

Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[Cl:16].[F:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1OB(O)O.[F-].[Cs+].O1CCOCC1>[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O>[Cl:16][C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[C:21]1[CH:20]=[CH:19][C:18]([F:17])=[CH:23][C:22]=1[F:24])=[CH:10][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:7]=2

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

Under argon gas atmosphere, a mixture of methyl 4-bromo-3-chloroquinoline-6-carboxylate (130 mg), 2,4-difluorophenylboric acid (137 mg), a 1,1′-bis(diphenylphosphino)ferrocene palladium (H) dichloride/dichloromethane complex (177 mg), cesium fluoride (197 mg), 1,4-dioxane (8 mL), and water (2 mL) was heated under stirring in an oil bath at 100° C. for one day. The reaction mixture was returned to room temperature, and water was added, and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified under silica gel column chromatography (hexane/ethyl acetate) to obtain methyl 3-chloro-4-(2,4-difluorophenyl)quinoline-6-carboxylate (100 mg).

Aufarbeitung

customwas returned to room temperature
extractionextracted with ethyl acetate
concentrationThe organic layer was concentrated under reduced pressure
customthe resulting residue was purified under silica gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag: ord-777a251daad84671af204320cfc450bb
Quelldatensatz: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08853242B2

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